Iodine-catalyzed oxidative cross-coupling of indoles and azoles: regioselective synthesis of N-linked 2-(azol-1-yl)indole derivatives

The Journal of Organic Chemistry
Danupat BeukeawSirilata Yotphan

Abstract

A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.

References

Apr 1, 2000·Bioorganic & Medicinal Chemistry Letters·H MoritaJ Kobayashi
Oct 2, 2001·The Journal of Organic Chemistry·J KobayashiH Morita
Aug 1, 2002·Journal of the American Chemical Society·Alec D LebsackBrian A Stearns
Feb 5, 2005·Natural Product Reports·Masanori Somei, Fumio Yamada
Jul 14, 2005·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Mar 10, 2006·Organic Letters·Liwen HeSteven L Castle
Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe
Apr 7, 2007·Angewandte Chemie·Mohammad Movassaghi, Michael A Schmidt
Apr 13, 2007·Organic Letters·Cong Liu, Ross A Widenhoefer
Jun 20, 2007·Chemical Society Reviews·Ilya V Seregin, Vladimir Gevorgyan
Jun 26, 2009·Angewandte Chemie·Bing MaSteven L Castle
Dec 1, 2009·Angewandte Chemie·Marco Bandini, Astrid Eichholzer
Dec 30, 2009·Journal of the American Chemical Society·Bing MaSteven L Castle
Jan 30, 2010·Angewandte Chemie·Stéphane BeaumontPhilippe Dauban
May 6, 2010·Journal of the American Chemical Society·Derek J SchipperKeith Fagnou
Dec 25, 2010·The Journal of Organic Chemistry·Ying-Xiu LiYong-Min Liang
Feb 15, 2011·Organic Letters·Arepalli Sateesh Kumar, Rajagopal Nagarajan
Jul 15, 2011·Organic Letters·Xue-Yuan LiuYong-Min Liang
Aug 27, 2011·The Journal of Organic Chemistry·Manjunath Lamani, Kandikere Ramaiah Prabhu
Jan 21, 2012·Chemical Communications : Chem Comm·Ying-Xiu LiYong-Min Liang
Mar 7, 2012·Chemical Reviews·Morteza Shiri
Aug 3, 2012·Angewandte Chemie·Jie-Sheng TianTeck-Peng Loh
Oct 9, 2012·Chemistry : a European Journal·Manjunath Lamani, Kandikere Ramaiah Prabhu
Oct 10, 2012·Organic & Biomolecular Chemistry·Ashok D PehereAndrew D Abell
Feb 5, 2013·The Journal of Organic Chemistry·Ulrich KloecknerBoris J Nachtsheim
Sep 14, 2013·Organic Letters·Zhong-Jian CaiShun-Jun Ji
Nov 29, 2013·Organic & Biomolecular Chemistry·Gao WangXiao-Qi Yu
Jan 23, 2014·Chemical Communications : Chem Comm·Yunhe LvQian Zhang
Mar 22, 2014·Chemical Communications : Chem Comm·Shan TangAiwen Lei
Apr 2, 2014·Chemical Communications : Chem Comm·Jingjing ZhaoFuwei Li
May 7, 2014·Chemical Communications : Chem Comm·Songjin GuoJiang Cheng
May 23, 2014·Organic & Biomolecular Chemistry·Xiao-Feng WuXinxin Qi

❮ Previous
Next ❯

Citations

Nov 5, 2015·Organic & Biomolecular Chemistry·Sirilata YotphanVichai Reutrakul
Feb 26, 2016·Organic & Biomolecular Chemistry·Pragati K PrasadArumugam Sudalai
Apr 14, 2017·The Journal of Organic Chemistry·Abhishek GuptaNidhi Jain
Jul 4, 2017·Chemical Communications : Chem Comm·Zhao-Ying YangBin Wang
Jun 21, 2019·Organic & Biomolecular Chemistry·Kunita Phakdeeyothin, Sirilata Yotphan
Feb 8, 2020·Topics in Current Chemistry·Bhaskar DekaPranjal K Baruah
Nov 14, 2020·Organic Letters·Ning LeiKe Zheng

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.